Monomer, high molecular compound and photosensitive composition

Abstract

A monomer represented by the following general formula (m-1): wherein R is a group having an alicyclic skeleton, R 2 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group, X 1 is a bivalent organic group containing a heteroatom, j is an integer of 0 to 3, and R 1 is a group selected from the following groups, a monovalent organic group having Si (R1-1), and —(X 2 ) k —R 4 —(X 3 ) m —C(R 6 ) 3   (R1-2), wherein X 2 and X 3 are a bivalent organic group containing a heteroatom, k and m are an integer of 0 to 3, R 4 is a bivalent alkyl group, R 6 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group.

What is claimed is:  
     
       1. A high molecular compound containing a repeating unit represented by the following general formula (u-1):                    
       wherein R 0  is an alicyclic group; X 0  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —O—, —OC(═O)—, or —OCH 2 C(═O)—, wherein R 3  is hydrogen atom, halogen atom, or hydrocarbon atom; R 2 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group; j is an integer of 0 to 3; R 100  is a group selected from the following groups;  
       a monovalent organic group having Si (R1-1), and  
       
         
           —(X 102 ) k —R 4 —(X 3 ) m —C(R 6 ) 3   (R11-2),  
         
       
       wherein X 102  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —OCH 2 C(═O)O—, —OSO 2 —, or —S(═O) 2 O—; k is an integer of [0] 1 to 3; R 4  is a bivalent alkyl group; X 3  is a bivalent organic group containing a heteroatom; m is an integer of 0 to 3; R 6 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group.  
     
     
       2. The high molecular compound according to claim  1 , wherein said repeating unit represented by the general formula (u-1) is included at a ratio of 5 mole % or more. 
     
     
       3. The high molecular compound according to claim  1 , wherein said high molecular compound has a softening point of 20° C. or more and a molecular weight of 500 to 900,000. 
     
     
       4. A high molecular compound containing a repeating unit represented by the following general formula (u-1):                    
       wherein R 0  is an alicyclic group; X 0  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —O—, —OC(═O)—, or —OCH 2 C(═O)—, wherein R 3  is hydrogen atom, halogen atom, or hydrocarbon atom; R 2 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group; j is an integer of 0 to 3; R 100  is a group selected from the following groups;  
       a monovalent organic group having Si (R1-1), and  
       
         
           —(X 102 ) k —R 4 —(X 3 ) m —C(R 6 ) 3   (R11-2),  
         
       
       wherein X 102  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —OCH 2 C(═O)O—, —OSO 2 —, or —S(═O) 2 —; k is an integer of 0 to 3; R 4  is a bivalent alkyl group; X 3  is a bivalent organic group containing a heteroatom; m is an integer of 1 to 3; R 6 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group.  
     
     
       5. The high molecular compound according to claim  4 , wherein said repeating unit represented by the general formula (u-1) is included at a ratio of 5 mole % or more. 
     
     
       6. The high molecular compound according to claim  4 , wherein said high molecular compound has a softening point of 20° C. or more and a molecular weight of 500 to 900,000. 
     
     
       7. A high molecular compound containing at least one kind of repeating unit represented by the following general formulas (u-2) and (u-3):                    
       wherein R is a group having an alicyclic skeleton; R 2 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group; X 1  is a bivalent organic group containing a heteroatom; j is an integer of 0 to 3; R 1  is a group selected from the following groups;  
       a monovalent organic group having Si (R1-1), and  
       
         
           —(X 2 ) k —R 4 —(X 3 ) 3 —C(R 6 ) 3   (R1-2),  
         
       
       wherein X 2  is a bivalent organic group containing a heteroatom; k is an integer of 0 to 3; R 4  is a bivalent alkyl group; X 3  is a bivalent organic group containing a heteroatom; m is an integer of 0 to 3; R 6 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group;  
       R 8 s may be the same or different and are individually hydrocarbon group, pentacycloalkyl group, tetracycloalkyl group, tricycloalkyl group, bicycloalkyl group, heterocycloalkyl group, or a group containing a terpenoid skeleton wherein at least one of R 8 s may be combined with part of R thereby to form a ring.  
     
     
       8. The high molecular compound according to claim  7 , wherein said repeating unit represented by the general formula (u-2) and (u-3) is included at a ratio of 5 mole % or more. 
     
     
       9. The high molecular compound according to claim  7 , wherein said high molecular compound has a softening point of 20° C. or more and a molecular weight of 500 to 900,000. 
     
     
       10. A photosensitive composition which comprises a high molecular compound containing a repeating unit represented by the following general formula (u-1); and a photo-acid generating agent:                    
       wherein R 0  is an alicyclic group; X 0  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —O—, —OC(═O)—, or —OCH 2 C(═O)—, wherein R 3  is hydrogen atom, halogen atom, or hydrocarbon atom; R 2 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group; j is an integer of 0 to 3;  
       R 100  is a group selected from the following groups;  
       a monovalent organic group having Si (R1-1), and  
       
         
           —(X 102 ) k —R 4 —(X 3 ) m —C(R 6 ) 3   (R11-2),  
         
       
       wherein X 102  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —OCH 2 C(═O)O—, —OS 2 —, or —S(═O) 2 O—; k is an integer of [0] 1 to 3; R 4  is a bivalent alkyl group; X 3  is a bivalent organic group containing a heteroatom; m is an integer of 0 to 3; R 6 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group.  
     
     
       11. The photosensitive composition according to claim  10 , wherein said high molecular compound comprises a group having an aromatic ring. 
     
     
       12. The photosensitive composition according to claim  11 , wherein said aromatic ring is naphthalene or a derivative thereof. 
     
     
       13. The photosensitive composition according to claim  10 , wherein said high molecular compound comprises a group exhibiting alkali-solubility through a decomposition thereof by an acid and/or an alkali soluble group. 
     
     
       14. The photosensitive composition according to claim  10 , wherein said high molecular compound comprises a group represented by the following chemical formula (7):                    
     
     
       15. The photosensitive composition according to claim  10 , wherein a compound represented by the following chemical formula (8) is included therein: 
       
         
           R 31 —X 31 —R 32   (8)  
         
       
       wherein R 31  is hydrogen atom, halogen atom or monovalent organic group; X 31  is a bivalent organic group having a heteroatom; and R 32  is a group having an alicyclic skeleton.  
     
     
       16. A photosensitive composition which comprises a high molecular compound containing a repeating unit represented by the following general formula (u-1); and a photo-acid generating agent:                    
       wherein R 0  is an alicyclic group; X 0  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —O—, —OC(═O)—, or —OCH 2 C(═O)—, wherein R 3  is hydrogen atom, halogen atom, or hydrocarbon atom; R 2 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group; j is an integer of 0 to 3;  
       R 100  is a group selected from the following groups;  
       a monovalent organic group having Si (R1-1), and  
       
         
           —(X 102 ) k —R 4 —(X 3 ) m —C(R 6 ) 3   (R11-2),  
         
       
       wherein X 102  is >C═O, —C(═O)O—, —C(═O)NR 3 —, —SO 2 —, —S(═O) 2 NR 3 —, —OCH 2 C(═O)O—, —OS 2 —, or —S(═O) 2 O—; k is an integer of 0 to 3; R 4  is a bivalent alkyl group; X 3  is a bivalent organic group containing a heteroatom; m is an integer of 1 to 3; R 6 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group.  
     
     
       17. The photosensitive composition according to claim  16 , wherein said high molecular compound comprises a group having an aromatic ring. 
     
     
       18. The photosensitive composition according to claim  17 , wherein said aromatic ring is naphthalene or a derivative thereof. 
     
     
       19. The photosensitive composition according to claim  16 , wherein said high molecular compound comprises a group exhibiting alkali-solubility through a decomposition thereof by an acid and/or an alkali soluble group. 
     
     
       20. The photosensitive composition according to claim  16 , wherein said high molecular compound comprises a group represented by the following chemical formula (7):                    
     
     
       21. The photosensitive composition according to claim  16 , wherein a compound represented by the following chemical formula (8) is included therein: 
       
         
           R 31 —X 31 —R 32   (8)  
         
       
       wherein R 31  is hydrogen atom, halogen atom or monovalent organic group; X 31  is a bivalent organic group having a heteroatom; and R 32  is a group having an alicyclic skeleton.  
     
     
       22. A photosensitive composition which comprises a high molecular compound containing at least one kind of repeating unit represented by the following general formulas (u-2) and (u-3); and a photo-acid generating agent:                    
       wherein R is a group having an alicyclic skeleton; R 2 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group; X 1  is a bivalent organic group containing a heteroatom; j is an integer of 0 to 3; R 1  is a group selected from the following groups;  
       a monovalent organic group having Si (R1-1), and  
       
         
           —(X 2 ) k —R 4 —(X 3 ) m —C(R 6  ) 3   (R1-2),  
         
       
       wherein X 2  is a bivalent organic group containing a heteroatom; k is an integer of 0 to 3; R 4  is a bivalent alkyl group; X 3  is a bivalent organic group containing a heteroatom; m is an integer of 0 to 3; R 6 s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group;  
       R 8 s may be the same or different and are individually hydrocarbon group, pentacycloalkyl group, tetracycloalkyl group, tricycloalkyl group, bicycloalkyl group, heterocycloalkyl group, or a group containing a terpenoid skeleton wherein at least one of R 8 s may be combined with part of R thereby to form a ring.  
     
     
       23. The photosensitive composition according to claim  22 , wherein said high molecular compound comprises a group having an aromatic ring. 
     
     
       24. The photosensitive composition according to claim  23 , wherein said aromatic ring is naphthalene or a derivative thereof. 
     
     
       25. The photosensitive composition according to claim  22 , wherein said high molecular compound comprises a group exhibiting alkali-solubility through a decomposition thereof by an acid and/or an alkali soluble group. 
     
     
       26. The photosensitive composition according to claim  22 , wherein said high molecular compound comprises a group represented by the following chemical formula (7):                    
     
     
       27. The photosensitive composition according to claim  22 , wherein a compound represented by the following chemical formula (8) is included therein; 
       
         
           R 31 —X 31 —R 32   (8)  
         
       
       wherein R 31  is hydrogen atom, halogen atom or monovalent organic group; X 31  is a bivalent organic group having a heteroatom; and R 32  is a group having an alicyclic skeleton.